Kovpak was born to a poor Ukrainian peasant family in Kotelva village in Kharkov Governorate, Russian Empire (in present-day Ukraine).

In the interwar period he was a head of the local government in the town of Putyvl, Sumy Oblast (province).

At the time of the German invasion of Soviet Ukraine partisan units led by Sydir Kovpak waged guerrilla warfare against Axis forces originally in partisan strongholds in Sumy and Bryansk regions but later its operation spread deep into German-occupied territory including Kyiv, Zhytomyr, Rivne, Homyel, Volyn and other regions.

Kovpak mastered guerrilla tactics and was awarded Hero of the Soviet Union title twice (1942;[2] 1944[3]).

According to the memoirs of his lieutenant Vershigora, his promotion and General's stars were airdropped to his partisan unit's position deep behind the front lines.